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First off, we know not everyone cares what guys think about their outfits—we fashionable ladies get dressed for ourselves, because looking good makes us feel good, too. But hey, we're still curious about what goes on in a dude's head when we cruise past in high-waisted pants or hit the town with a bright fuchsia-slicked pout. Love it? Hate it? Couldn't care less?

We had to ask, and since we wanted thoughtful, sincere answers from guys who really get personal style, we went straight to the most well-dressed, sartorially-savvy Washingtonians we know. DJs, clothing designers, photographers, and editors—each one weighed in with nuggets of fashion wisdom that ranged from helpful to hilarious. Even if you don't take their advice, we guarantee you'll be surprised by it.